September in Connecticut means cooler nights, changing leaves, and weekends packed with community celebrations. From hometown fairs and cultural festivals to Oktoberfest weekends filled with food and music, there’s something for everyone to enjoy. Here’s a guide to what’s happening across Connecticut — with plenty right here in Fairfield County.
🌾 Agricultural Fairs & State Traditions
Connecticut’s fair season is in full swing this September, with classic events that highlight local farming, food, crafts, and live entertainment.
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Sept 4–7 – Hebron Harvest Fair | Hebron
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Sept 4–7 – North Haven Fair | North Haven
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Sept 4–7 – Wapping Fair | South Windsor
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Sept 5–7 – Norwalk Oyster Festival | Norwalk (Veteran’s Memorial Park)
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Sept 5–7 – Bethlehem Fair | Bethlehem
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Sept 11–14 – Four Town Fair | Somers
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Sept 11–14 – Berlin Lions Agricultural Fair | Berlin
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Sept 12–14 – Assumption Church Fair | Fairfield
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Sept 19–21 – Guilford Fair | Guilford
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Sept 25–28 – Durham Fair | Durham
🎪 Community & Family Festivals
Beyond the fairgrounds, local towns celebrate community spirit with food, music, and family-friendly fun.
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Sept 5 – 45th Annual Fall Festival | Easton
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Sept 6 – Slice of Saugatuck Festival | Westport
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Sept 7 – Westport Dog Festival | Westport (Winslow Park)
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Sept 13–14 – Maritime Heritage Festival | Mystic Seaport
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Aug 31 – Oct 20 (weekends) – Connecticut Renaissance Faire | Lebanon
🍺 Oktoberfest Celebrations
September also kicks off Connecticut’s Oktoberfest season, with craft beer, traditional food, and plenty of live entertainment.
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Sept 6–7 – Tribus Fest | Milford – Free Oktoberfest weekend with steins, festbier & live music
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Sept 13 – Fairfield Oktoberfest | Fairfield (FTC/Sanford St Lot) – Seasonal beers, food trucks, games, axe throwing
✨ From oyster shucking on the Norwalk waterfront to sipping a seasonal brew in Fairfield, September is the perfect time to explore everything Connecticut has to offer. Grab your friends, bring the family, and enjoy a month full of traditions, food, and fall fun.